Allyl bromide → (1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate

HRID 331096ノート

反応式

HRID 331096 の反応式
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[Cl-].[NH4+].Br[CH2:20][CH:21]=[CH2:22]>C1COCC1.[Zn]>[CH2:22]([C:2]1([OH:1])[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1)[CH:21]=[CH2:20]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 86668857(R)-benzyl 3-oxocyclopentanecarboxylate

生成物 1

HCID 86668862(1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate収率 48.6%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of (R)-benzyl 3-oxocyclopentanecarboxylate (1 g, 4.58 mmol) in THF (10 mL) was added zinc powder (2.098 mL, 229 mmol), saturated aqueous ammonium chloride solution (20 mL) followed by 3-bromoprop-1-ene (1.663 g, 13.75 mmol) slowly at room temperature. The resulting mixture was heated to 80° C. for 3 hours, then allowed to stir at room temperature for additional 12 hours. The reaction mixture was filtered and the filtrate concentrated. To the residue was added ethyl acetate (20 mL) and the resulting mixture was washed with water (5 ml), brine (5 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate (580 mg, 2.228 mmol, 48.6% yield) as an oil. It was used as such for the next step without further purification. MS (ESI+) m/z 283 (M+Na)+

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. additionTo the residue was added ethyl acetate (20 mL)
  4. washthe resulting mixture was washed with water (5 ml), brine (5 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e1e97ce7d2d34f45965b4e1cc1ddc9e7
出典データセット
uspto-grants-2014_11
特許番号
US08877749B2

反応ノート

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